The present invention relates to novel pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultural/horticultural fungicides containing said derivatives as the active ingredients.
As compounds related to the pyrimidinylbenzimidazole derivatives of the present invention, 4-aminopyrimidine derivatives disclosed as pharmaceuticals in U.S. Pat. No. 5,525,604 and European Patent No. 640,599 and pyrimidine derivatives disclosed as herbicides in International Publication No. WO94/17059, are mentioned, but no disclosure regarding agricultural/horticultural fungicides has been made. French Patent No. 1,476,529 discloses benzimidazolyl sulfonamide derivatives having insecticidal and fungicidal activities, but no disclosure regarding the present compounds has been made. Further, as compounds related to the triazinylbenzimidazole derivatives of the present invention, triazine derivatives disclosed in JP-A-47-36837, JP-A-49-17677 and Kogyo Kagaku Zassi (Journal of Industrial Chemistry) vol 73, No. 5, p1000 (1970) as coloring agents for textile goods, may be mentioned, but no disclosure regarding agricultural/horticultural fungicides has been made. Further, anilinopyrimidine derivatives as production intermediates therefor have not been known.
The present invention provides novel pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultural/horticultural fungicides containing them as the active ingredients.
The present inventors have conducted extensive studies to create novel agricultural/horticultural fungicides and as a result, found that the pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives of the present invention (hereinafter referred to as compounds of the present invention) are novel compounds which are not disclosed in any literatures and have outstanding effects as agricultural/horticultural fungicides, and the present invention has been accomplished.
Namely, the present invention resides in a pyrimidinylbenzimidazole or triazinylbenzimidazole derivative represented by the general formula [I]: 
wherein A is N or CR3, each of R1 and R2 which are independent of each other, is a hydrogen atom, a halogen atom, a (C1-C6) alkyl group, a (C2-C6) alkenyl group, a (C2-C6) alkynyl group, a (C3-C6) cycloalkyl group, a (C1-C4) haloalkyl group, a (C1-C6) alkoxy group, a (C2-C6) alkenyloxy group, a (C2-C6) alkynyloxy group, a (C3-C6) cycloalkoxy group, a (C1-C4) haloalkoxy group, a cyano (C1-C4) alkyloxy group, a (C1-C4) alkoxy (C1-C4) alkyloxy group, a (C3-C6) cycloalkyl (C1-C4) alkoxy group, a benzyloxy group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], a (C1-C6) alkylthio group, a (C1-C4) alkoxy (C1-C4) alkyl group, a phenoxy group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], a (C1-C4) alkylcarbonyl group, a formyl group, a phenyl group, a di(C1-C4) alkylamino group, a cyano group or a (C1-C6) alkylsulfonyl group, R3 is a hydrogen atom, a (C1-C6) alkyl group, a (C1-C6) alkoxy group or a halogen atom, X is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a (C1-C6) alkyl group, a (C2-C6) alkenyl group, a (C2-C6) alkynyl group, a (C3-C6) cycloalkyl group, a benzyl group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], a (C1-C6) alkoxy group, a (C2-C6) alkenyloxy group, a (C2-C6) alkynyloxy group, a (C1-C6) alkylthio group, a (C1-C6) alkylsulfonyl group, a phenoxy group, a (C1-C4) alkoxy (C1-C4) alkyl group, a (C1-C4) haloalkyl group, a (C1-C4) haloalkoxy group, a (C1-C4) alkylcarbonyl group, a (C1-C4) alkoxycarbonyl group, an amino group, a mono(C1-C4) alkylamino group, a di(C1-C4) alkylamino group, an anilino group or a phenyl group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], Y is a halogen atom, a nitro group, a cyano group, a (C1-C6) alkyl group, a (C2-C6) alkenyl group, a (C2-C6) alkynyl group, a (C1-C6) alkoxy group, a (C2-C6) alkenyloxy group, a (C2-C6) alkynyloxy group, a (C1-C4) haloalkoxy group, a (C1-C6) alkylthio group, a (C1-C4) alkoxy (C1-C4) alkyl group, a (C1-C4) haloalkyl group, a (C1-C4) alkylcarbonyl group, a (C1-C4) alkoxycarbonyl group, a benzoyl group, an amino group, a mono(C1-C4) alkylamino group, a di(C1-C4) alkylamino group, a phenyl group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group] or a phenoxy group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], and n is 0 or an integer of from 1 to 3}, an anilinopyrimidine or anilinotriazine derivative, as an intermediate therefor, represented by the general formula [XV]: 
(wherein A is N or CR3, each of R1 and R2 which are independent of each other, is a hydrogen atom, a halogen atom, a (C1-C6) alkyl group, a (C2-C6) alkenyl group, a (C2-C6) alkynyl group, a (C3-C6) cycloalkyl group, a (C1-C4) haloalkyl group, a (C1-C6) alkoxy group, a (C2-C6) alkenyloxy group, a (C2-C6) alkynyloxy group, a (C3-C6) cycloalkoxy group, a (C1-C4) haloalkoxy group, a cyano (C1-C4) alkyloxy group, a (C1-C4) alkoxy (C1-C4) alkyloxy group, a (C3-C6) cycloalkyl (C1-C4) alkoxy group, a benzyloxy group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], a (C1-C6) alkylthio group, a (C1-C4) alkoxy (C1-C4) alkyl group, a phenoxy group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], a (C1-C4) alkylcarbonyl group, a formyl group, a phenyl group, a di(C1-C4) alkylamino group, a cyano group or a (C1-C6) alkylsulfonyl group, R3 is a hydrogen atom, a (C1-C6) alkyl group, a (C1-C6) alkoxy group or a halogen atom, R5 is an amino group, a nitro group or xe2x80x94NHCOX, X is a hydrogen atom, a halogen atom, a nitro group, a cyano group, a (C1-C6) alkyl group, a (C2-C6) alkenyl group, a (C2-C6) alkynyl group, a (C3-C6) cycloalkyl group, a benzyl group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], a (C1-C6) alkoxy group, a (C2-C6) alkenyloxy group, a (C2-C6) alkynyloxy group, a (C2-C6) alkylthio group, a (C1-C6) alkylsulfonyl group, a phenoxy group, a (C1-C4) alkoxy (C1-C4) alkyl group, a (C1-C4) haloalkyl group, a (C1-C4) haloalkoxy group, a (C1-C4) alkylcarbonyl group, a (C1-C4) alkoxycarbonyl group, an amino group, a mono(C1-C4) alkylamino group, a di(C1-C4) alkylamino group, an anilino group or a phenyl group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], Y is a halogen atom, a nitro group, a cyano group, a (C1-C6) alkyl group, a (C2-C6) alkenyl group, a (C2-C6) alkynyl group, a (C1-C6) alkoxy group, a (C2-C6) alkenyloxy group, a (C2-C6) alkynyloxy group, a (C1-C4) haloalkoxy group, a (C1-C6) alkylthio group, a (C1-C4) alkoxy (C1-C4) alkyl group, a (C1-C4) haloalkyl group, a (C1-C4) alkylcarbonyl group, a (C1-C4) alkoxycarbonyl group, a benzoyl group, an amino group, a mono(C1-C4) alkylamino group, a di(C1-C4) alkylamino group, a phenyl group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group] or a phenoxy group [said group may be substituted by a halogen atom, a (C1-C4) alkyl group or a (C1-C4) alkoxy group], and n is 0 or an integer of from 1 to 3}, and an agricultural/horticultural fungicide containing the pyrimidinylbenzimidazole or triazinylbenzimidazole derivative as the active ingredient.
Now, the symbols and terms used in the present specification will be explained below.
The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
A notation such as (C1-C6) indicates that the carbon number of a substituent following this notation is from 1 to 6 in this case.
The (C1-C6) alkyl group is a linear or branched alkyl group and may, for example, be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl or 3,3-dimethylbutyl.
The (C3-C6) cycloalkyl may, for example, be cyclopropyl, cyclopentyl or cyclohexyl.
The (C1-C4) haloalkyl group is a linear or branched alkyl group substituted by a halogen atom and may, for example, be fluoromethyl, chloromethyl, difluoromethyl, dichloromethyl, trifluoromethyl or pentafluoroethyl.
The (C2-C6) alkenyl group is a linear or branched alkenyl group and may, for example, be vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-butenyl or 2-butenyl.
The (C2-C6) alkynyl group is a linear or branched alkynyl group and may, for example, be ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 4-methyl-1-pentynyl or 3-methyl-1-pentynyl.
The (C1-C6) alkoxy group is an alkyloxy group wherein the alkyl moiety has the above meaning and may, for example, be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentyloxy or n-hexyloxy.
The (C2-C6) alkenyloxy group is an alkenyloxy group wherein the alkenyl moiety has the above meaning, and may, for example, be allyloxy, isopropenyloxy or 2-butenyloxy.
The (C2-C6) alkynyloxy group is an alkynyloxy group wherein the alkynyl moiety has the above meaning, and may, for example, be 2-propynyloxy, 2-butynyloxy or 3-butynyloxy.
The (C3-C6) cycloalkoxy group is a cycloalkyloxy group wherein the cycloalkyl moiety has the above meaning, and may, for example, be cyclopropyloxy, cyclopentyloxy or cyclohexyloxy.
The (C1-C4) haloalkoxy group is a haloalkyloxy group wherein the haloalkyl moiety has the above meaning, and may, for example, be fluoromethoxy, difluoromethoxy, trifluoromethoxy or pentafluoroethoxy.
The (C1-C6) alkylthio group is an alkylthio group wherein the alkyl moiety has the above meaning, and may, for example, be methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butylthio, tert-butylthio or n-hexylthio.
The (C3-C6) cycloalkyl (C1-C4) alkoxy group may, for example, be cyclopropylmethyloxy, cyclopentylmethyloxy or cyclohexylmethyloxy.
The (C1-C4) alkoxy (C1-C4) alkyl group is a group wherein the alkyl moiety and the alkoxy moiety have the above meanings, and may, for example, be a group such as methoxymethyl, ethoxymethyl, isopropoxymethyl, pentyloxymethyl, methoxyethyl or butoxyethyl.
The (C1-C4) alkoxy (C1-C4) alkyloxy group is a group wherein the alkyl moiety and the alkoxy moiety have the above meanings, and may, for example, be a group such as methoxymethyloxy, ethoxymethyloxy, isopropoxymethyloxy, pentyloxymethyloxy, methoxyethyloxy or butoxyethyloxy.
The cyano (C1-C4) alkyloxy group is a group wherein the alkyl moiety has the above meaning, and may, for example, be a group such as cyanomethyloxy, cyanoethyloxy or cyanopropyloxy.
The (C1-C4) alkylcarbonyl group is an alkylcarbonyl group wherein the alkyl moiety has the above meaning, and may, for example, be a group such as acetyl, propionyl, butyryl, isobutyryl, pivaloyl or hexanoyl.
The (C1-C4) alkoxycarbonyl group is an alkoxycarbonyl group wherein the alkoxy moiety has the above meaning, and may, for example, be methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, sec-butoxycarbonyl, tert-butoxycarbonyl, n-pentyloxycarbonyl or n-hexyloxycarbonyl.
The mono (C1-C4) alkylamino group is a monoalkylamino group wherein the alkyl moiety has the above meaning, and may, for example, be methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, sec-butylamino, tert-butylamino or n-hexylamino.
The di (C1-C4) alkylamino group may, for example, be dimethylamino, diethylamino, dipropylamino or dibutylamino.
The (C1-C6) alkylsulfonyl group is an alkylsulfonyl group wherein the alkyl moiety has the above meaning, and may, for example, be methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl or n-hexylsulfonyl.
Now, specific examples of the compounds of the present invention represented by the general formula [I] will be disclosed in Tables 1 to 35. However, the compounds of the present invention are not limited to such compounds. Here, the compound numbers will be referred to in the subsequent description.
Symbols in the Tables have the following meanings respectively. Me represents methyl, Et represents ethyl, Pr represents n-propyl, Pr-i represents isopropyl, Bu represents n-butyl, Pr-c represents cyclopropyl, Pn-c represents cyclopentyl, Ph represents phenyl, and Bn represents benzyl. Further, Ph(2-Cl) represents 2-chlorophenyl, and Bn(4-Cl) represents 4-chlorobenzyl, for example.
Typical processes for producing pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives represented by the general formula [I] as the compounds of the present invention, will be exemplified below. 
(wherein X, Y, R1, R2, A and n have the same meanings as mentioned above respectively, and L is a leaving group such as a halogen atom, a (C1-C6) alkylsulfonyl group or a benzylsulfonyl group.)
The compound of the present invention represented by the general formula [I] can be produced by reacting a benzimidazole derivative represented by the general formula [II] and a pyrimidine derivative or triazine derivative represented by the general formula [III] in the presence of a base in a solvent. Here, as the base, a carbonate, hydrogencarbonate, acetate, alcoholate, hydroxide, hydride or oxide of an alkali metal or alkaline earth metal, particularly sodium, potassium, magnesium or calcium, may, for example, be used. The solvent which can be used in the present reaction may be one which does not inhibit the progress of the present reaction, and an ether such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme or diglyme, a halogenated hydrocarbon such as dichloroethane, chloroform, carbon tetrachloride or tetrachloroethane, an aromatic hydrocarbon such as benzene, chlorobenzene, nitrobenzene or toluene, or N,N-dimethylformamide, N,N-dimethylacetoamide, 1,3-dimethyl-2-imidazolinone or dimethylsulfoxide, may, for example, be used. These inert solvents may be used alone or as mixed. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the inert solvent to be used, and preferably within a range of from 0xc2x0 C. to 80xc2x0 C. The reaction time varies depending upon e.g. the reaction temperature and the reaction amount, but may be selected within a range of from 1 hour to 48 hours in general. After completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires.
Here, the benzimidazole derivative represented by the general formula [II] may be a commercially available product or may be produced by a known method [e.g. a method as disclosed in Angewandte Chemie, vol 85, p866 (1973); Journal of the American Chemical Society, vol 69, p2459 (1947); Journal of the American Chemical Society, vol 82, p3138 (1960); Organic Syntheses, vol 2, p65 (1943); or Organic Syntheses, vol 4, p569 (1963)]. 
(wherein X, Y, R1, R2, A and n have the same meanings as mentioned above respectively.)
The anilide derivative represented by the general formula [V] can be produced by reacting an anilinopyrimidine derivative or anilinotriazine derivative represented by the general formula [IV] with an acylating agent in an inert solvent. The reaction is carried out preferably in the presence of a base. As the acylating agent, an acid halide such as acetyl chloride, propionyl chloride or benzoyl chloride, or an acid anhydride such as trifluoroacetic anhydride, propionic anhydride or benzoic anhydride may be mentioned. The inert solvent which can be used in the present reaction may be one which does not inhibit the progress of the present reaction, and for example, e.g. a ketone such as acetone, methyl ethyl ketone or cyclohexanone, an ether such as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, monoglyme or diglyme, an ester such as ethyl acetate or methyl acetate, a halogenated hydrocarbon such as dichloroethane, chloroform, carbon tetrachloride or tetrachloroethane, an aromatic hydrocarbon such as benzene, chlorobenzene, nitrobenzene or toluene, a nitrile such as acetonitrile, or N,N-dimethylformamide, N,N-dimethylacetoamide, 1,3-dimethyl-2-imidazolinone, dimethylsulfoxide, pyridine or water, may be used. These inert solvents may be used alone or as mixed. As the base to be used in the present reaction, an inorganic base or an organic base may be used. For example, as an inorganic base, a carbonate or hydroxide of an alkali metal or alkaline earth metal, such as sodium carbonate, potassium carbonate, calcium carbonate, sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide or calcium hydroxide, or a hydride of an alkali metal such as lithium hydride or sodium hydride, may be used, and as an organic base, triethylamine, diisopropylethylamine or pyridine may, for example, be used. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the inert solvent to be used, and preferably within a range of from 0xc2x0 C. to 50xc2x0 C. The reaction time varies depending upon e.g. the reaction temperature and the reaction amount, but may be selected within a range of from several minutes to 48 hours in general.
Then, the anilide derivative represented by the general formula [V] is subjected to a cyclization reaction without a solvent or in a solvent, in the presence of a catalyst as the case requires, to produce the compound of the present invention represented by the general formula [I]. As the catalyst to be used here, an inorganic acid such as sulfuric acid or hydrochloric acid or an organic acid such as para-toluenesulfonic acid may, for example, be used. As the solvent which can be used in the present reaction, the solvent exemplified in Process 1 may be used. The reaction temperature may be selected within a range of from 0xc2x0 C. to the boiling point of the solvent to be used, and preferably within a range of from room temperature to the boiling point of the solvent. The reaction time varies depending upon e.g. the reaction temperature and the reaction amount, but may be selected within a range of from 1 hour to 48 hours in general. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires. 
(wherein X, Y, R1, R2, A and n have the same meanings as mentioned above respectively.)
The compound of the present invention represented by the general formula [I] can be produced directly by heating an anilinopyrimidine derivative or anilinotriazine derivative represented by the general formula [IV] in a carboxylic acid represented by the general formula [VI], in the presence of an acid anhydride as the case requires. The reaction temperature may be selected within a range of from 0xc2x0 C. to the boiling point of the carboxylic acid to be used, preferably within a range of from room temperature to the boiling point of the carboxylic acid. The reaction time may be selected within a range of from 1 hour to 48 hours in general. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires. 
(wherein Y, R1, R2, A and n have the same meanings as mentioned above respectively.)
The compound represented by the general formula [I-a] can be produced by reacting an anilinopyrimidine derivative or anilinotriazine derivative represented by the general formula [IV] and a reagent [VII] such as BrCN or H2NCN by a method known from a literature [e.g. a method as disclosed in Journal of the American Chemical Society, vol 69, p2459 (1947); or Angewandte Chemie, vol 85, p866 (1973)] in a solvent. As the solvent which can be used in the present reaction, the solvent as exemplified in Process 1 may be used. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the reaction mixture to be used, preferably within a range of from 0xc2x0 C. to the boiling point of the reaction mixture. The reaction time varies depending upon e.g. the reaction temperature or the reaction amount, and may be selected within a range of from 1 hour to 48 hours in general. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires. 
(wherein Xxe2x80x2 is a halogen atom, and Y, R1, R2, A and n have the same meanings as mentioned above respectively.)
The compound represented by the general formula [I-d] can be produced by diazotizing a 2-aminobenzimidazole derivative represented by the general formula [I-a] by a known method [e.g. Sandmeyer method, Schwechten method or Gattermann method] in a solvent at a reaction temperature which are conventionally employed, followed by halogenation. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires. 
(wherein Y, R1, R2, A and n have the same meanings as mentioned above respectively, and R4 is a C1-C6 alkyl group.)
The compound represented by the general formula [I-e] can be produced by oxidizing a pyrimidinylbenzimidazole derivative or triazinylbenzimidazole derivative represented by the general formula [I-b] by a known method. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires. The oxidizing agent which can be used in the present reaction may, for example, be hydrogen peroxide or an organic peracid such as m-chloroperbenzoic acid. As the solvent which can be used, the solvent as exemplified in Process 1 may be used. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the reaction mixture to be used, preferably within a range of from 5xc2x0 C. to the boiling point of the reaction mixture. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires. 
(wherein Y, R1, R2, A, L and n have the same meanings as mentioned above respectively, and Xxe2x80x3 is a (C1-C6) alkoxy, (C2-C6) alkenyloxy, (C2-C6) alkynyloxy, (C1-C6) alkylthio or (C1-C6) alkylamino group.)
The compound of the present invention represented by the general formula [I-f] can be produced by reacting a pyrimidinylbenzimidazole derivative or triazinylbenzimidazole derivative represented by the general formula [I-c] and an alcohol, mercaptan or amine represented by the general formula [XVI] in the presence of a base without a solvent or in a solvent. As the base and the solvent which can be used in the present reaction, the base and the solvent as exemplified in Process 1 may be used. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the reaction mixture to be used, preferably within a range of from room temperature to the boiling point of the reaction mixture. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires. 
(wherein X, Y, A, L and n have the same meanings as mentioned above respectively, and Z is a (C1-C6) alkoxy, (C2-C6) alkenyloxy, (C2-C6) alkynloxy, (C1-C6) alkylthio or di (C1-C6) alkylamino group.)
The compound of the present invention represented by the general formula [I-h] can be produced by reacting a pyrimidinylbenzimidazole derivative or triazinylbenzimidazole derivative represented by the general formula [I-g] and an alcohol, mercaptan or amine represented by the general formula [VIII] in the presence of a base without a solvent or in a proper solvent. As the base and the solvent which can be used in the present reaction, the base and the solvent as exemplified in Process 1 may be used. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the reaction mixture to be used, preferably within a range of from room temperature to the boiling point of the reaction mixture. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires. 
(wherein Y, R1, R2, A and n have the same meanings as mentioned above respectively.)
The compound of the present invention represented by the general formula [I-i] can be produced by reducing an anilinotriazine derivative represented by the general formula [IX] with iron powder in acetic acid or in a mixed solvent of acetic anhydride and acetic acid. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the reaction mixture to be used, preferably within a range of from room temperature to the boiling point of the reaction mixture. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires.
Now, processes for synthesizing the production intermediates for the compounds of the present invention will be explained in detail below.
Synthesis of Production Intermediate Represented by the General Formula [IV]
The compound [IV] may be synthesized, for example, in accordance with the following process, but the process is not limited thereto. 
(wherein Y, R1, R2, A, L and n have the same meanings as mentioned above respectively.)
A formanilide derivative represented by the general formula [X] and a pyrimidine derivative or triazine derivative represented by the general formula [III] are reacted in the presence of a base in an inert solvent at a reaction temperature within a range of from xe2x88x9220xc2x0 C. to the boiling point of the solvent, preferably within a range of from room temperature to 80xc2x0 C., followed by hydrolysis with e.g. an acid such as hydrochloric acid, hydrobromic acid or sulfuric acid or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide by a generally known method to obtain [XI]. Then, the obtained [XI] is reduced with a reducing agent such as iron, tin chloride, or a hydrogen atom accompanied with another catalyst such as palladium carbon or Raney Nickel, by a generally known method to produce an anilinopyrimidine derivative or anilinotriazine derivative represented by the general formula [IV].
Synthesis of Production Intermediate Represented by the General Formula [XI-b]
The compound [XI-b] may be synthesized, for example, in accordance with the following process, but the process is not limited thereto. 
(wherein Y, Z and n have the same meanings as mentioned above respectively.)
A nitroaniline derivative represented by the general formula [XII] and cyanuric chloride represented by [XIII] are reacted in the presence of a base without a solvent or in a proper solvent to produce an anilinotriazine derivative represented by the general formula [XI-a], which is successively reacted with an alcohol, mercaptan or amine represented by the general formula [VIII] in the presence of a base without a solvent or in a proper solvent to produce an anilinotriazine derivative represented by the general formula [XI-b]. As the base and the solvent which can be used in the present reaction, the base and the solvent as exemplified in Process 1 may be used. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the reaction mixture to be used, preferably within a range of from room temperature to the boiling point of the reaction mixture. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires.
Synthesis of Production Intermediates Represented by the General Formulae [XI-c] and [XI-d]
The compounds [XI-c] and [XI-d] may be synthesized, for example, in accordance with the following process, but the process is not limited thereto. 
(wherein R1, Y, L, Z and n have the same meanings as mentioned above respectively.)
A formanilide derivative represented by the general formula [X] and a triazine derivative represented by [XIV] are reacted in the presence of a base without a solvent or in a proper solvent, followed by hydrolysis with e.g. an acid such as hydrochloric acid, hydrobromic acid or sulfuric acid or an alkali metal hydroxide such as sodium hydroxide or potassium hydroxide, by a generally known method to produce an anilinotriazine derivative represented by the general formula [XI-c], which is successively reacted with an alcohol, mercaptan or amine represented by the general formula [VIII] in the presence of a base without a solvent or in a proper solvent to produce an anilinotriazine derivative represented by the general formula [XI-d]. As the base and the solvent which can be used in the present reaction, the base and the solvent as exemplified in Process 1 may be used. The reaction temperature may be selected within a range of from xe2x88x9220xc2x0 C. to the boiling point of the reaction mixture to be used, preferably within a range of from room temperature to the boiling point of the reaction mixture. After the completion of the reaction, the desired product is isolated from the reaction system by a conventional method and may be purified by e.g. column chromatography or recrystallization, as the case requires.
Here, the anilinopyrimidine and anilinotriazine derivatives represented by the general formulae [IV], [V] and [XI] are also novel compounds, and specific examples in thereof will be disclosed in Tables 36 to 65.